Sodium Carbonate → ethyl 4-[[1-[(2-methyl-4-thiazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate

HRID 2379040Notes

Reaction equation

HRID 2379040 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.Cl.Cl[CH2:24][C:25]1[N:26]=[C:27]([CH3:30])[S:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C(=O)C>O>[CH3:30][C:27]1[S:28][CH:29]=[C:25]([CH2:24][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:26]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl ester

Product 1

HCID 18957838ethyl 4-[[1-[(2-methyl-4-thiazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylateYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.9 parts of ethyl 4-[(1H-benzimidazol-2-yl)amino]-1-piperidinecarboxylate, 1.8 parts of 4-(chloromethyl)-2-methylthiazole monohydrochloride, 2.12 pans of sodium carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at 70° C. The reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated and the residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.5 parts (37.5%) of ethyl 4-[[1-[(2-methyl-4-thiazolyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinecarboxylate; mp. 160° C. (comp. 12).

Workup

  1. extractionthe product was extracted with 4-methyl-2-pentanone
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was crystallized from acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-d79bf2bd6b794fddbc4b4c965f53879f
Source dataset
uspto-grants-1994_11
Patent number
US05360807

Reaction notes

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